I don’t smoke anything anymore (had to stop if I was going to quit cigarettes. I don’t regret the choice but I don’t begrudge you wanting to try), but I think I wrote up a couple of posts that cover this exact topic back when I was a pipe smoker.
Let me touch on some things mentioned in this thread before I go off searching for them:
Smoking tobacco is, frequently, very different than smelling it. This is very true. It also takes a bit of practice to pack and smoke a pipe in such a way that it isn’t a hot and bitter tongue burning experience. But, it’s not that hard to learn.
Borkram Riff has a very very distinctive flavor/scent that a lot of people do not like and if you are one of those people it will ruin your pipe. It has a strong tendency to “ghost” pipes, which is not a bad thing if you have a rotation of pipes and dedicate one pipe to a particular tobacco, but if you are only going to have one or two pipes is something that should be avoided.
Eventually old or estate pipes are something you might want to look into, but they have their own issues. For now get something new and deal with breaking it in. The break in period has more to do with making the pipe smoke cooler so that you don’t actually burn a hole in it than anything anyway, and less to do with the smoking experience.
Do rest your pipes if they are briar. This has less to do with getting them too hot and more to do with making sure the wood dries completely. If they are clay or corncob this is not an issue. Smoke those all day long every day (corncobs need a bit of drying time in theory, but are really forgiving.)
Which brings me to my suggestion for a first pipe. A Missouri Meerschaum company corncob. Only buy MM cobs, since most others are pretty crap, but MM makes fantastic pipes. Just remember that all the advice for briar pipes doesn’t work for cobs. You want to treat them like clay or meerschaum and keep them very very clean with no cake (we can talk about cake later.)
Do get pipe cleaners and a pipe tool, both are essential. Also get yourself some wood match sticks, mostly because they make lighting the pipe easier than lighters (which can be tricky to light a pipe with and not burn yourself.)
Flavored tobaccos are popular because they smell great, but tend to bite (burn your tongue). That said, there are some great “drugstore” tobaccos that have that nostalgic smell and don’t bite so much. Carter Hallwould be my top recommendation. Prince Albert is pretty good too, as is Half and Half. Stay away from Capt. Black and anything cherry flavored, at least for now.
More later after I do some searching.
ETA: oh and, pipes are fussy, but that’s part of the point. They take care and patience to learn how to use. You have to fiddle with them to keep them lit, and even then they go out and you will have to relight. That’s ok, that’s the point. It’s not about the quick nic hit like a cigarette, it’s about spending an hour or so doing something active that is also relaxing. As a hobby it’s sort of like knitting mixed with espresso drinking.
Also it’s easy to do cheaply, but it can become a very spendy habit. I gave away my tobaccos when I quit smoking, but I still have all 40 or so of my pipes.